Hydrochloric Acid → HCID 178426847, compound

HRID 246854Notes

Reaction equation

HRID 246854 reaction equation
[ClH:1].C([O:9][C:10]1[C:11]([CH3:24])=[C:12]([NH:17][C:18]([NH:20][C:21](=[NH:23])[NH2:22])=[O:19])[C:13]([CH3:16])=[CH:14][CH:15]=1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[ClH:1].[CH3:24][C:11]1[C:10]([OH:9])=[CH:15][CH:14]=[C:13]([CH3:16])[C:12]=1[NH:17][C:18]([NH:20][C:21](=[NH:22])[NH2:23])=[O:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178426831HCID 178426831, compound

Product 1

HCID 178426847HCID 178426847, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(3-benzyloxy-2,6-dimethylphenyl)-3-amidinourea hydrochloride (17.4 g) and 5% Pd/C (1.0 g) in absolute ethanol (200 ml) containing 50 ml of methanolic HCl is shaken under an atmosphere of H2 (50 psi) for 45 minutes. The reaction mixture is filtered through Celite and the Celite washed with methanol. The filtrate is concentrated in vacuo and the foam taken up in acetonitrile. The acetonitrile solution is concentrated in vacuo and the residue crystallized from methanol/acetonitrile to give, after filtering and vacuum drying, 10.1 grams of the 3-hydroxy phenyl amidinourea hydrochloride salt , M.P. 207°-208° C. (dec).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. washthe Celite washed with methanol
  3. concentrationThe filtrate is concentrated in vacuo
  4. concentrationThe acetonitrile solution is concentrated in vacuo
  5. customthe residue crystallized from methanol/acetonitrile
  6. customto give
  7. filtrationafter filtering
  8. customvacuum drying

Sources & evidence

ORD record
ord-1c000f5e9e8c49dcb1a7cf8abe8427b8
Source dataset
uspto-grants-1987_11
Patent number
US04704401

Reaction notes

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